HCID 11279119, compound → HCID 9840899, compound

HRID 651389Notes

Reaction equation

HRID 651389 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1>[Pd].CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11279119HCID 11279119, compound

Product 1

HCID 9840899HCID 9840899, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A warm solution of 2-(4′-fluorophenyl)-4-[4′-(1-dimethylamino-2-propyn-3-yl)phenyl]thiazole (0.2 g, 0.6 mmol) in abs. EtOH (20 mL) containing a catalytic amount of palladium on activated carbon (5%, 20 mg) is shaked under hydrogen atomsphere (30 psi) for 2 h. After removal of the catalyst by filtration, the filtrate is concentrated to give 2-(4′-fluorophenyl)-4-[4′-(3-N,N-dimethylaminopropyl)phenyl]thiazole as desired product (0.18 g, 89%) 1H NMR (CDCl3): δ 1.65 (m, 2H), 2.24 (s, 6H), 2.32 (t, 2H), 2.69 (t, 2H), 7.14 (t, 2H), 7.27 (d, 2H), 7.40 (s, 1H), 7.89 (d, 2H), 8.02 (m, 2H).

Workup

  1. customfor 2 h
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-819293b9c55d42e88b6315f226a4092f
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

Loading…